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Synthesis of Oligoquinoline Dendronized Fullerenes for Potential Use in Organic Photovoltaic Devices
Kwon, Tae-Woo,Jenekhe, Samson A. Korean Chemical Society 2012 Bulletin of the Korean Chemical Society Vol.33 No.8
New C60 fullerenes derivatives [G1]-C60 (1) and [G2]-C60 (2) comprising of phenylenevinylene bridges and phenylquinoline peripheral surface groups were synthesized by 1,3-dipolar cycloaddition reaction of fullerene C60 with azomethine ylide in situ generated from [Gx]-CHO dendrons (x = 1 and 2) and sarcosine.
Synthesis of Oligoquinoline Dendronized Fullerenes for Potential Use in Organic Photovoltaic Devices
권태우,Samson A. Jenekhe 대한화학회 2012 Bulletin of the Korean Chemical Society Vol.33 No.8
New C60 fullerenes derivatives [G1]-C60 (1) and [G2]-C60 (2) comprising of phenylenevinylene bridges and phenylquinoline peripheral surface groups were synthesized by 1,3-dipolar cycloaddition reaction of fullerene C60 with azomethine ylide in situ generated from [Gx]-CHO dendrons (x = 1 and 2) and sarcosine.
이호준,Hao Xin,박성민,박석일,안택,박동규,Samson A. Jenekhe,권태우 대한화학회 2012 Bulletin of the Korean Chemical Society Vol.33 No.5
The coupling reaction between 5-bromo-3-phenylbenzo[c]isoxazole and diphenylamine followed by further condensation with a mono-, di- or ter-acetyl aromatic compound in the presence of diphenyl phosphate at 145 oC gave a novel asymmetric diarylquinolines, oligoquinolines with diphenylamine endgroups, and a first generation quinoline dendrimer in 41-82% isolated yield. The electrochemical and photophysical properties of the oligoquinolines were characterized by cyclic voltammograms (CVs) and spectroscopy. All the quinolines emit bright sky blue light due to charge transfer from quinoline group to diphenly amine with very high quantum efficiency (> 90%). Organic light-emitting diodes (OLEDs) were fabricated using these quinolines as emitting materials. Among different device architectures explored, OLEDs with a structure of ITO/PEDOT (40 nm)/TAPC (15 nm)/D-A quinoline (40 nm)/TPBI (30 nm)/LiF (1 nm)/Al using TAPC as an electron blocking layer and TPBI as a hole blocking layer gave the best performance. A high external quantum efficiency in the range of 1.2-2.3% were achieved in all the quinolines with the best performance in BBQA(5). Our results indicate diarylamino-substituted oligoquinoline and dendrimer are promising materials for OLEDs applications.
Kim, Kimyung,Park, Min Soo,Na, Yaena,Choi, Jongwan,Jenekhe, Samson A.,Kim, Felix Sunjoo Elsevier 2019 ORGANIC ELECTRONICS Vol.65 No.-
<P><B>Abstract</B></P> <P>Polystyrene-grafted alumina nanoparticles were synthesized by silane coupling between dimethylchlorosilane-terminated polystyrene (PS) and gamma-type alumina nanoparticles and characterized. The surface grafting density of the polystyrene chains on the nanoparticles was estimated to be 0.13 molecules per square nanometer. The Al<SUB>2</SUB>O<SUB>3</SUB>-PS nanoparticles are solution processable in organic solvents, including ethyl acetate, butyl acetate, and toluene, which enabled preparation of blends with polystyrene or poly (methyl methacrylate). The dielectric constant of the Al<SUB>2</SUB>O<SUB>3</SUB>-PS nanoparticle/polymer blend films is composition tunable from 2.59 to 7.79. The alumina-PS nanoparticles and their blends with polymers were found to form efficient surface passivation films on the oxide dielectric layer in organic field-effect transistors (OFETs).</P> <P><B>Highlights</B></P> <P> <UL> <LI> Polystyrene-grafted alumina core-shell nanoparticles were synthesized through simple silane coupling and the processability in various organic solvents was improved. </LI> <LI> Structure, electrical properties, composite film formation of alumina-PS nanoparticles were characterized. </LI> <LI> Alumina-PS nanoparticles were applied as a surface modification agent in organic field-effect transistors. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Murari, N.M.,Hwang, Y.J.,Kim, F.S.,Jenekhe, S.A. Elsevier Science 2016 ORGANIC ELECTRONICS Vol.31 No.-
<P>Charge trapping is an undesirable phenomenon and a common challenge in the operation of n-channel organic field-effect transistors. Herein, we exploit charge trapping in an n-type semiconducting poly (naphthalene diimide-alt-biselenophene) (PNDIBS) as the key operational mechanism to develop high performance, nonvolatile, electronic memory devices. The PNDIBS-based field-effect transistor memory devices were programmed at 60 V and they showed excellent charge-trapping and de-trapping characteristics, which could be cycled more than 200 times with a current ratio of 10(3) between the two binary states. Programmed data could be retained for 10(3) s with a memory window of 28 V. This is a record performance for n-channel organic transistor with inherent charge-trapping capability without using external charge trapping agents. However, the memory device performance was greatly reduced, as expected, when the n-type polymer semiconductor was end-capped with phenyl groups to reduce the trap density. These results show that the trap density of n-type semiconducting polymers could be engineered to control the inherent charge-trapping capability and device performance for developing high-performance low-cost memory devices. (c) 2016 Elsevier B.V. All rights reserved.</P>
Lee, Ho-Joon,Xin, Hao,Park, Seong-Min,Park, Seog-Il,Ahn, Taek,Park, Dong-Kyu,Jenekhe, Samson A.,Kwon, Tae-Woo Korean Chemical Society 2012 Bulletin of the Korean Chemical Society Vol.33 No.5
The coupling reaction between 5-bromo-3-phenylbenzo[c]isoxazole and diphenylamine followed by further condensation with a mono-, di- or ter-acetyl aromatic compound in the presence of diphenyl phosphate at $145^{\circ}C$ gave a novel asymmetric diarylquinolines, oligoquinolines with diphenylamine endgroups, and a first generation quinoline dendrimer in 41-82% isolated yield. The electrochemical and photophysical properties of the oligoquinolines were characterized by cyclic voltammograms (CVs) and spectroscopy. All the quinolines emit bright sky blue light due to charge transfer from quinoline group to diphenly amine with very high quantum efficiency (> 90%). Organic light-emitting diodes (OLEDs) were fabricated using these quinolines as emitting materials. Among different device architectures explored, OLEDs with a structure of ITO/PEDOT (40 nm)/TAPC (15 nm)/D-A quinoline (40 nm)/TPBI (30 nm)/LiF (1 nm)/Al using TAPC as an electron blocking layer and TPBI as a hole blocking layer gave the best performance. A high external quantum efficiency in the range of 1.2-2.3% were achieved in all the quinolines with the best performance in BBQA(5). Our results indicate diarylamino-substituted oligoquinoline and dendrimer are promising materials for OLEDs applications.
Shin, Won Suk,Joo, Moon-Kyu,Kim, Sung Chul,Park, Sung-Min,Jin, Sung-Ho,Shim, Jong-Min,Lee, Jin Kook,Lee, Jae Wook,Gal, Yeong-Soon,Jenekhe, Samson A. Royal Society of Chemistry 2006 Journal of materials chemistry Vol.16 No.42
<P>Five new thermally robust electroluminescent arylenevinylene conjugated polymers, including poly[3′,6′-bis(3,7-dimethyloctyloxy)-9,9′-spirobifluorenyl-2,7-vinylene] <B>[(OC<SUB>10</SUB>)<SUB>2</SUB>-Spiro-PFV]</B> and poly[{3′,6′-bis(3,7-dimethyloctyloxy)-9,9′-spirobifluorenyl-2,7-vinylene}-<I>co</I>-2-{methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene}] <B>[(OC<SUB>10</SUB>)<SUB>2</SUB>-Spiro-PFV-<I>co</I>-MEH-PPV]</B>, were synthesized and used to fabricate efficient light-emitting diodes (LEDs). The glass transition temperatures of the polymers were found to be higher than those of PPVs and PFs, and are in the range 170–222 °C. ITO/PEDOT/Polymer/LiF/Al LEDs containing the new polymers were found to have emission colors that vary from blue (467 nm) to yellow (587 nm) depending on the copolymer composition. The maximum brightness and luminance efficiency of these LEDs were found to be up to 4062 cd m<SUP>−2</SUP> and 1.79 cd A<SUP>−1</SUP> respectively.</P> <P>Graphic Abstract</P><P>Five new thermally robust electroluminescent arylenevinylene conjugated polymers, including <B>(OC<SUB>10</SUB>)<SUB>2</SUB>-Spiro-PFV</B> and <B>(OC<SUB>10</SUB>)<SUB>2</SUB>-Spiro-PFV-<I>co</I>-MEH-PPV</B>, were synthesized and used to fabricate efficient light-emitting diodes (LEDs). <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=b607944j'> </P>
High‐Performance n‐Channel Thin‐Film Field‐Effect Transistors Based on a Nanowire‐Forming Polymer
Hahm, Suk Gyu,Rho, Yecheol,Jung, Jungwoon,Kim, Se Hyun,Sajoto, Tissa,Kim, Felix S.,Barlow, Stephen,Park, Chan Eon,Jenekhe, Samson A.,Marder, Seth R.,Ree, Moonhor WILEY‐VCH Verlag 2013 Advanced functional materials Vol.23 No.16
<P><B>Abstract</B></P><P>A new electrontransport polymer, poly{[<I>N,N′</I>‐dioctylperylene‐3,4,9,10‐bis(dicarboximide)‐1,7(6)‐diyl]‐<I>alt</I>‐[(2,5‐bis(2‐ethyl‐hexyl)‐1,4‐phenylene)bis(ethyn‐2,1‐diyl]} (PDIC8‐EB), is synthesized. In chloroform, the polymer undergoes self‐assembly, forming a nanowire suspension. The nanowire's optical and electrochemical properties, morphological structure, and field‐effect transistor (FET) characteristics are investigated. Thin films fabricated from a PDIC8‐EB nanowire suspension are composed of ordered nanowires and ordered and amorphous non‐nanowire phases, whereas films prepared from a homogeneous PDIC8‐EB solution consist of only the ordered and amorphous non‐nanowire phases. X‐ray scattering experiments suggest that in both nanowires and ordered phases, the PDIC8 units are laterally stacked in an edge‐on manner with respect to the film plane, with full interdigitation of the octyl chains, and with the polymer backbones preferentially oriented within the film plane. The ordering and orientations are significantly enhanced through thermal annealing at 200 °C under inert conditions. The polymer film with high degree of structural ordering and strong orientation yields a high electron mobility (0.10 ± 0.05 cm<SUP>2</SUP> V<SUP>−1</SUP> s<SUP>−1</SUP>), with a high on/off ratio (3.7 × 10<SUP>6</SUP>), a low threshold voltage (8 V), and negligible hysteresis (0.5 V). This study demonstrates that the polymer in the nanowire suspension provides a suitable material for fabricating the active layers of high‐performance n‐channel FET devices via a solution coating process.</P>